Hike the Appalachian Trail in Connecticut; 7 Different Hikes

View on Lions Head Hike Salisbury Connecticut Appalachian Trail
Lions Head View, Salisbury

Are you looking for hikes to do on the Appalachian Trail in Connecticut? Hikes with views, stone walls, waterfalls, rivers, and streams along the way? Fields of green and grassy meadows on one side of a well-worn narrow path with the Housatonic River on the other?! 💦⛰

A classic New England hiking experience awaits you along the 50 miles of the Appalachian Trail where you’ll find several mountains in Connecticut in the northwest corner of the state. 🌲

In 2020, Jared, the dogs, and I hiked the whole AT in CT by breaking it into 7 different hikes.

In this post I will show you these 7 moderate day hikes including maps and All Trails links 🔗 for each so you can navigate yourself while you’re out there!

Of course, the 50 miles can be broken up a bunch of different ways; some people might even hike it in 2 days! True story 👀 I ran into a group that was trail running the entire thing in one day! I like hiking to be challenging yet enjoyable, so moderately sized hikes for me, please! ⬇️

🗺 About the Appalachian Trail

➡️ Did you know that the Appalachian Trail is the longest (at 2,193 miles) hiking-only footpath in the whole world, running from Georgia to Maine?!

And we are so lucky to have a portion of it in our state of CT..

The Appalachian Trail runs through the northwest corner of CT and is about an hour and 20 minutes from Hartford so wherever you are located in Connecticut, you can make these hikes a day trip destination.

To me, living in Farmington, CT it’s worth the drive because some the very best views in the state are on the AT!

📝Important Note:

These are all 2 car, point-to-point hikes, meaning you leave one car at the start and one at the ending point so you don’t have to hike all the way back. 🚗🚙

If you are hiking solo then you will need to double your miles and hike back!

🥾How to do a point-to-point hike:

First drive to the ending point and leave a car parked there. Then hop in the other car with your hiking partner and drive and park at the starting point. You are now ready to begin your Appalachian Trail Connecticut journey! 🥾

The hikes are listed in order, south to north, but you may reverse the order and hike north to south if you’d like. Click on each underlined location below to pull up the AllTrails map I made so that you can save & follow on AllTrails. 😊

50 miles of the Appalachian Trail Split into 7 Different Hikes

(In order from south to north…)

1. CT Appalachian Trail Leg 1: Hoyt Road to Bull’s Bridge, Gaylordsville ~4 miles, 800 ft of elevation gain

This is the first hike along the Appalachian Trail in Connecticut. You are treated to nicely laid rocks for stairs and a little incline at the start before you come down to the Housatonic River.

Look out for Tenmile hill shelter in a wide open field if you want a shady spot for lunch.

The bridge you cross has just a few steps up to it but it is a little steep. Once over the bridge you can stop for a quick break by the river. You’ll then continue the final stretch of this hike with the rushing Housatonic River on your right.

There is no big peak with views here, the water is the main attraction! It is a great start and welcome to your journey along the AT in CT. 🥾

2. CT Appalachian Trail Leg 2: Bull’s Bridge to Macedonia Rd, South Kent ~7.3 miles, 1900 ft of elevation

A big chunk of the incline on this hike is right in the beginning. So try not to eat too much on the ride over and save your snacks for the nice view right after the initial climb!

Climb up about 800 ft and you reach the top of Schaghtichoke Mountain which offers sweeping southeast views.

You will stay up at this elevation for the most part walking along with minor dips here and there, a stream crossing, and a tent site. The descent to the road is a little steep but you’ll be glad to see your car and complete this second leg of the journey. 🐾

3. CT Appalachian Trail Leg 3 Macedonia Rd to River Rd, Kent ~4.7 miles, 1362 ft of elevation gain

You’ll love the start of this hike. Entering a big field that takes you across a little stream and lets you settle in before you begin a little climb of 500 feet in 0.4 miles that will get your heart pumping.

The highlight of this hike is for sure Caleb’s Peak with wide open views to the east and then also St John’s Ledges which you will walk along at the end of the hike which also has views.

The slabs are slabs of rock (that you walk along) are about 100 feet high and are named after their owner in the 1800s, Timothy St Johns. (Check out my full post on hiking St John’s Ledges here.)

4. CT Appalachian Trail Leg 4 River Road to Pine Knob Loop Trail, West Cornwall ~8.45 miles, 1400 ft

If you love narrow paths that hug and run alongside a river, then you’ll love this stretch of trail! This is the longest stretch of the Appalachian Trail that runs right along the Housatonic River.

Taking you through a wide open field with mountain views on the left, the river will be on your right and it will be stay there for a good few miles!

In fact, the first 4.5 miles of this hike is pretty flat and then after that you will hike up some elevation and at the end come down along the raging falls at Pine Knob Loop. 💦

5. CT Appalachian Trail Leg 5 Pine Knob to Sharon Mountain to Rt 7, Salisbury ~10.7 miles, ~2600 ft of elevation gain

This is a big one so pack lots of snacks and water!

You’ll start with almost 600 ft of elevation gain here which takes you up to Pine Knob Lookout (great place to watch the sunrise)! Continuing on you’ll have several ups and downs until you get to Sharon Mountain.

This is another great view and good place to sit as long as you don’t mind the sound of the racing cars below at Lime Rock Park! You will definitely feel a sense of accomplishment after this hike and hopefully have lots of beautiful pictures to go through. 📸⛰

6. CT Appalachian Trail Leg 6 Route 7 to 44 Salisbury ~8.46 miles, 1400 ft of elevation gain

This hike might become one of your favorites as it combines a bridge crossing with a waterfall sighting and 2 views!

One of which seems to come out of nowhere. You’ll start by walking along a quiet road in Amesville, crossing a bridge and seeing a top waterfall in CT called Great Falls!

After this, you will begin a long, steady climb up to Mount Prospect. Take in the views here but don’t spend all your free time in this spot because a little while later you will run into one of the best and most unique views in CT, Rand’s View.

What makes it so special is how you come upon it, emerging from the woods to a view so wide, a panorama shot wouldn’t do it justice! After this, keep your eye out for and get a picture with Giant’s Thumb, and then continue the rest of the (relatively flat) way to the car.

⭐️I have a full post you can find on Rand’s View that offers 3 different routes to get to it, including just a 2-mile round trip hike!! Check it out in this post here.⭐️

7. CT Appalachian Trail Leg 7 Rt 44 to Bear Mountain ⛰ 7.2 miles, 1900 ft of elevation gain

On the final leg of our Appalachian Trail in Connecticut journey, you have a bit of a steady climb but you’re treated to two peaks; Bear Mountain (the tallest mountain in CT) and Lion’s Head.

And like a bear, you will kind of be using all fours here to reach these two peaks! 🐻

Part of the trail that takes you up to Bear Mountain goes through Mount Riga State Park in Salisbury, CT. But before you get to the tallest mountain in CT, you will see and enjoy the eastern-facing views at Lion’s Head. 🦁 Lions, tigers, and bears!! Oh my..

There is a steep but short scramble right before you reach Lion’s Head and then you will experience a similar climbing experience on the way down from Bear Mountain’s summit. I love bringing a hiking pole (or two) to help brace myself on the way up or down these steep sections.

After Lion’s Head, you’ll head to Bear Mountain and be sure to climb the pile of rocks there and see the views in the distance. 

(If you’d like to explore 2 other routes and hikes up to Bear Mountain (both shorter than the one listed above) then click to see my post on hiking Bear!)

👏That’s it, friends! By now, if you’ve hiked the whole Appalachian Trail in Connecticut!

You’re probably tired, hungry, and hopefully with a camera full of memories! There are lots of hikes out there in CT and New England but it feels great to complete a whole section of a trail.

While it’s not the whole Appalachian Trail it sure is one beautiful chunk of it! If you’d like more info on the AT you can check out this site here. And if you are ready to tackle amazing hikes in other states (like 10 Best Hikes in New Hampshire) be sure to head over to my Northeast Travel tab on homepage!

Please let me know if you complete any of these! I would love to see your pictures or hear about your experience. Leave a comment below or if you do hike and post about it on Instagram, tag me so I can see. 😍 And if you have any questions, write them below or you can message me on instagram. 📨

Wherever your hiking boots take you next time I hope you have fun, enjoy the journey, and take a few pics along the way! 

Happy Trails… 💖🥾🐾🐾 ⛰

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